CN111620785B - Continuous chlorination method of nitroaniline - Google Patents
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Abstract
The invention discloses a continuous chlorination method of nitroaniline, which comprises the following steps: adding nitroaniline and sulfuric acid into a dissolving unit for dissolving; (2) Continuously inputting the obtained solution and chlorine into a mixing unit respectively, mixing, flowing into a delay reaction tube for chlorination reaction, and dividing the obtained reaction material into a backflow material and a finished material through a circulating unit; (3) And (3) refluxing the reflux material obtained in the step (2) to a dissolving unit to mix and circulate with nitroaniline, recovering redundant chlorine and hydrogen chloride gas generated in the reaction from the material through a gas collecting unit, cooling, crystallizing and separating to obtain a solid product chloronitroaniline, and circulating mother liquor to the dissolving unit for dissolving the nitroaniline. The invention constructs a material circulation system, promotes the reaction system to be changed from heterogeneous phase to homogeneous phase, realizes high selectivity and high efficiency of continuous reaction, and reduces the production cost.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a continuous chlorination method of nitroaniline.
Background
Chloronitroaniline such as o-chloro-p-nitroaniline and 2,4-dinitro-6-chloroaniline is an important dye intermediate, and the main production method is the chlorination of nitroaniline. The prior chlorination process of nitroaniline is mainly carried out in a reaction kettle, hydrochloric acid is adopted as a medium, and a chlorinating agent is added in the pulping process for chlorination reaction. However, the conventional kettle type stirring cannot achieve a good mass and heat transfer effect, and local overhigh temperature and unbalanced material proportion are easily caused, so that a byproduct is generated.
In response to this problem, several patents propose continuous production processes to effect the chlorination of nitroaniline. The patent CN105461572B discloses a process for continuously synthesizing 2,4-dinitro-6-chloroaniline, which adopts multi-stage series reaction kettles, continuously adds raw materials into the reaction kettles, performs chlorination reaction under the stirring condition, and obtains products after continuous multi-kettle operation. Patent CN105461571B provides a process for continuously synthesizing 2,6-dichloro-p-nitroaniline, and a multistage series-connected reaction kettle is utilized to realize continuous production of 2,6-dichloro-p-nitroaniline. However, the reaction kettle has poor mass and heat transfer effects, and a side reaction problem still exists in a part of regions. CN104003888B proposes a preparation method of 2,4-dinitro-6-chloroaniline, a tubular reactor is adopted, 2,4-dinitroaniline and hydrochloric acid are conveyed into the reactor in an emulsion form, and a chlorinating agent sodium chlorate is input at the same time, so that the continuous synthesis of 2,4-dinitro-6-chloroaniline is realized. However, in the above method, two steps of reaction are required after the materials are mixed, and the sodium chlorate and hydrochloric acid generate chlorine to further react with 2,4-dinitroaniline, so that the overall reaction rate is reduced, and the generation of chlorine easily affects the uniformity and stability of the original emulsion. Meanwhile, the solubility of nitroaniline and chlorinated nitroaniline in hydrochloric acid is poor, and the control of the reaction process and the selection of a reaction window are negatively influenced; hydrochloric acid is easy to volatilize at a higher temperature, and the generated hydrogen chloride gas can reduce the stability of the reaction environment and interfere the reaction of chlorine gas and 2,4-dinitroaniline. The above factors make the stability, selectivity and efficiency of the reaction difficult to compromise in the conventional nitroaniline chlorination process.
Disclosure of Invention
Aiming at the defects in the field, the invention provides a continuous chlorination method of nitroaniline, which eliminates medium interference by introducing stable reaction medium sulfuric acid, reduces the reaction equivalent of chlorine by circulating materials, enables the chlorine to be dissolved in a solution, and enables the phase state of a reaction system to enter a homogeneous phase region from a two-phase region, thereby realizing the aims of high selectivity and high efficiency.
A continuous process for the chlorination of nitroaniline comprising the steps of:
(1) Adding nitroaniline and sulfuric acid into a dissolving unit for dissolving;
(2) Continuously inputting the obtained solution and chlorine into a mixing unit respectively, mixing, flowing into a delay reaction tube for chlorination reaction, and dividing the obtained reaction material into a backflow material and a finished material through a circulating unit;
(3) And (3) refluxing the reflux material obtained in the step (2) to the dissolving unit to replace sulfuric acid and mix with nitroaniline, recovering redundant chlorine and hydrogen chloride gas generated in the reaction from the finished material through a gas collecting unit, cooling, crystallizing and separating to obtain a solid product chloronitroaniline, and circulating the mother liquor to the dissolving unit to replace sulfuric acid for dissolving the nitroaniline.
According to the invention, through deep research on phase state conversion and reaction dynamics rules of a nitroaniline chlorination reaction system, a material circulation system is innovatively constructed, the reaction system is promoted to be converted from heterogeneous phase to homogeneous phase, the reaction controllability is greatly improved, the high selectivity and high efficiency of continuous reaction are realized, and the production cost is reduced.
Preferably, the nitroaniline in the dissolving unit is p-nitroaniline, o-nitroaniline or 2,4-dinitroaniline.
Preferably, the mass ratio of nitroaniline to sulfuric acid in the dissolving unit is 1:1-12, the mass concentration of the sulfuric acid is 85-100%, and the temperature of the obtained solution is 10-95 ℃. The sulfuric acid as a reaction medium can be kept stable in a wider temperature range, and no redundant gas is generated to interfere the chlorination reaction, so that the uniformity of a liquid phase reaction system is ensured.
In order to ensure the accuracy and stability of chlorine feeding under the condition of lower flow rate, preferably, the chlorine in the mixing unit is fed by controlling the feeding flow rate through a chlorine flow meter, and the pressure of a chlorine feeding pipeline is stabilized through a pressure regulating valve. Further preferably, the chlorine flowmeter is a mass flow meter.
Preferably, the molar ratio of nitroaniline to chlorine in the mixing unit is 1.5-2. The above-mentioned preferred amounts of chlorine ensure the conversion of nitroaniline.
Preferably, the mixing unit is used for mixing materials through a micro-mixing reactor or a super-gravity reactor, the mixing temperature is 10-100 ℃, and the mixing pressure is 0.1-1.1 MPa.
Preferably, in the step (2), the reaction temperature of the chlorination reaction is 10-100 ℃, the reaction pressure is 0.1-1.0 MPa, and the retention time of the materials in the delayed reaction tube is 0.5-5 h.
According to the invention, through circulating reflux, the reaction equivalent of the newly added nitroaniline and chlorine in the whole reaction system is controlled at a lower level, and the high-efficiency mixing performance of a micro-mixing reactor or a super-gravity reactor in a mixing unit is further combined, so that the gas-phase chlorine can be quickly absorbed by the liquid-phase reaction solution, and the reaction is promoted to enter a homogeneous system.
The preferred flow ratio of the reflux material to the finishing material is 2-15. Further research finds that the high flow ratio is favorable for improving the product quality, and the low flow ratio is favorable for improving the reaction efficiency, so that in order to better consider the product quality and the reaction efficiency, the flow ratio of the reflux material to the finishing material is further preferably 7-13. The split ratio is the flow ratio of the return material to the finishing material.
Preferably, the circulation unit divides the reaction material into a reflux material and a completion material by using a three-way valve.
The circulation unit can regulate and control the flow dividing ratio of the backflow material and the finished material through a flow regulating valve of a backflow material pipeline according to an online test result.
Preferably, the gas collection unit recovers chlorine gas and hydrogen chloride gas by a flash evaporation method. The mother liquor after cooling, crystallization, separation and recovery can be directly used for dissolving the nitroaniline of the welding unit.
In the step (3), the temperature of the cooling crystallization is preferably-10-40 ℃, more preferably-10 ℃, and the lower crystallization temperature is favorable for the rapid precipitation of the material from the solution, and the final product is obtained through solid-liquid separation and water washing.
Compared with the prior art, the invention has the main advantages that:
(1) The invention reduces the reaction equivalent of chlorine, simultaneously circulates a large amount of reaction liquid, and uses the microreactor on a circulation line to mix gas and liquid raw materials, thereby ensuring that the chlorine is quickly and uniformly absorbed, leading the phase state of a reaction system to enter a homogeneous phase region from a two-phase region, eliminating the influence of phase state change and leading the chlorine to be completely converted in the reactor.
(2) By adopting the conditions of the invention, the two raw materials are continuously and quantitatively added, and the reaction is rapidly started through high-efficiency mixing, so that the low selectivity caused by uneven mass and heat transfer is avoided, the controllability of the reaction is further improved, and the reaction is favorably expanded.
(3) The stable reaction medium sulfuric acid is introduced in the process, so that the uniformity of a liquid phase reaction environment is ensured, the homogeneous chlorination reaction of the solution is realized, and the mother solution can be directly recycled after the product is separated out; in addition, if the product is not separated out, the reaction material can be directly used for subsequent diazotization without post-treatment processes such as washing, drying and the like, and the potential of seamless connection between the process and a downstream process is shown.
Drawings
FIG. 1 is a schematic flow diagram of the continuous chlorination process of nitroaniline according to the present invention.
Detailed Description
The invention is further described with reference to the following drawings and specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The following examples are conducted under conditions not specified, usually according to conventional conditions, or according to conditions recommended by the manufacturer.
The continuous chlorination method of nitroaniline is shown in figure 1, and comprises the following steps:
(1) Adding nitroaniline and sulfuric acid into a dissolving unit for dissolving;
(2) Continuously inputting the obtained solution and chlorine into a mixing unit respectively, mixing, flowing into a delay reaction tube for chlorination reaction, and dividing the obtained reaction material into a backflow material and a finished material through a circulating unit;
(3) And (3) refluxing the reflux material obtained in the step (2) to the dissolving unit to replace sulfuric acid and mix with nitroaniline, wherein sulfuric acid does not need to be additionally added, the finished material is used for recovering redundant chlorine and hydrogen chloride gas generated in the reaction through a gas collecting unit, then cooling, crystallizing and separating to obtain a solid product chloronitroaniline, and mother liquor is circulated to the dissolving unit to replace sulfuric acid for dissolving nitroaniline.
Example 1
Dissolving 2,4-dinitroaniline in 98wt% sulfuric acid to obtain a sulfuric acid solution of 2,4-dinitroaniline, wherein the mass ratio of 2,4-dinitroaniline to 98wt% sulfuric acid is 1; the solution and chlorine are respectively conveyed to a micro-mixing reactor through an advection pump and a gas flowmeter, and the molar ratio of 2,4-dinitroaniline to chlorine is 1.60; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 50 ℃, the pressure is 0.4MPa, and the retention time is 2h; dividing the material obtained by the reaction into a backflow material and a finished material by a flow division ratio 7:1 through a circulation unit three-way valve; conveying the reflux material to a micro-mixing reactor, and mixing the reflux material with reaction raw materials; and (3) passing the completed material flow through a gas collection unit, recovering redundant chlorine and hydrogen chloride generated in the reaction, cooling to 0 ℃, crystallizing and separating a product from the solution, further performing solid-liquid separation to obtain 2,4-dinitro-6-chloroaniline, and circularly replacing sulfuric acid with the mother liquor for dissolving the nitroaniline. The product was analyzed by chromatography with a purity of 97.1% and a yield of 97.0%.
Example 2
Dissolving paranitroaniline in 95wt% sulfuric acid to obtain a sulfuric acid solution of the paranitroaniline, wherein the mass ratio of the paranitroaniline to the 95wt% sulfuric acid is 1:3, and the temperature of the solution is controlled at 35 ℃; the solution and chlorine are respectively conveyed to a supergravity reactor through an advection pump and a gas flowmeter, and the molar ratio of the paranitroaniline to the chlorine is 1; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 35 ℃, the pressure is 0.2MPa, and the retention time is 2.5h; dividing the material obtained by the reaction into a backflow material and a finished material by a flow division ratio 8:1 through a circulation unit three-way valve; conveying the reflux material to a supergravity reactor, and mixing the reflux material with reaction raw materials; and (3) passing the completed material flow through a gas collection unit, recovering redundant chlorine and hydrogen chloride generated in the reaction, cooling to 2 ℃, crystallizing and separating a product from the solution, further performing solid-liquid separation to obtain the o-chloro-p-nitroaniline, and circularly replacing sulfuric acid with the mother solution for dissolving the nitroaniline. The product was analyzed by chromatography with a purity of 98.5% and a yield of 98.2%.
Example 3
Dissolving p-nitroaniline in 98wt% sulfuric acid to obtain a sulfuric acid solution of the p-nitroaniline, wherein the mass ratio of the p-nitroaniline to the 98wt% sulfuric acid is 1:3, and the temperature of the solution is controlled at 75 ℃; the solution and chlorine are respectively conveyed to a micro-mixing reactor through an advection pump and a gas flowmeter, and the molar ratio of the paranitroaniline to the chlorine is 1.10; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 75 ℃, the pressure is 0.7MPa, and the retention time is 4.5h; the material obtained by the reaction is divided into a backflow material and a finished material by a circulation unit three-way valve according to a flow division ratio of 11; conveying the reflux material to a micro-mixing reactor, and mixing the reflux material with reaction raw materials; and (3) allowing the completed material flow to pass through a gas collection unit, recovering redundant chlorine and hydrogen chloride generated in the reaction, cooling to-5 ℃, crystallizing and separating a product from the solution, further performing solid-liquid separation to obtain 2,6-dichloro-4-nitroaniline, and circularly replacing sulfuric acid with the mother liquor for dissolving the nitroaniline. The product was analyzed by chromatography with a purity of 96.1% and a yield of 95.8%.
Example 4
Dissolving p-nitroaniline in 98wt% sulfuric acid to obtain a sulfuric acid solution of the p-nitroaniline, wherein the mass ratio of the p-nitroaniline to the 98wt% sulfuric acid is 1; the solution and chlorine are respectively conveyed to a micro-mixing reactor through an advection pump and a gas flowmeter, and the molar ratio of the paranitroaniline to the chlorine is 1; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 39 ℃, the pressure is 0.2MPa, and the retention time is 2.5h; dividing the material obtained by the reaction into a backflow material and a finished material through a circulation unit three-way valve according to a split ratio of 7:1; conveying the reflux material to a micro-mixing reactor, and mixing the reflux material with reaction raw materials; and (3) allowing the completed material flow to pass through a gas collection unit, recovering redundant chlorine and hydrogen chloride generated in the reaction, cooling to 0 ℃, crystallizing and separating a product from the solution, further performing solid-liquid separation to obtain the o-chloro-p-nitroaniline, and circularly replacing sulfuric acid with the mother liquor to dissolve the nitroaniline. The product was analyzed by chromatography with 98.0% purity and 97.8% yield.
Example 5
Dissolving p-nitroaniline in 93wt% sulfuric acid to obtain a sulfuric acid solution of the p-nitroaniline, wherein the mass ratio of the p-nitroaniline to the 93wt% sulfuric acid is 1:4, and the temperature of the solution is controlled at 78 ℃; the solution and chlorine are respectively conveyed to a micro-mixing reactor through an advection pump and a gas flowmeter, and the molar ratio of the paranitroaniline to the chlorine is 1.09; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 80 ℃, the pressure is 0.7MPa, and the retention time is 4h; the materials obtained by the reaction are divided into backflow materials and finished materials by a flow division ratio of 12; conveying the reflux material to a micro-mixing reactor, and mixing the reflux material with reaction raw materials; and (3) allowing the completed material flow to pass through a gas collection unit, recovering redundant chlorine and hydrogen chloride generated in the reaction, cooling to-1 ℃, crystallizing and separating a product from the solution, further performing solid-liquid separation to obtain 2,6-dichloro-4-nitroaniline, and circularly replacing sulfuric acid with the mother liquor for dissolving the nitroaniline. The product was analyzed by chromatography with a purity of 96.5% and a yield of 96.1%.
Example 6
2,4-dinitroaniline is dissolved in 96wt% sulfuric acid to obtain a sulfuric acid solution of 2,4-dinitroaniline, the mass ratio of 2,4-dinitroaniline to 96wt% sulfuric acid is 1:3, and the solution temperature is controlled to be 53 ℃; the solution and chlorine are respectively conveyed to a micro-mixing reactor through an advection pump and a gas flowmeter, and the molar ratio of 2,4-dinitroaniline to chlorine is 1.58; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 54 ℃, the pressure is 0.4MPa, and the retention time is 2h; dividing the material obtained by the reaction into a backflow material and a finished material by a flow division ratio 7:1 through a circulation unit three-way valve; conveying the reflux material to a micro-mixing reactor, and mixing the reflux material with reaction raw materials; and (3) allowing the material flow to pass through a gas collection unit, recovering redundant chlorine and hydrogen chloride generated in the reaction, cooling to 0 ℃, crystallizing and separating a product from the solution, further performing solid-liquid separation to obtain 2,4-dinitro-6-chloroaniline, and circularly replacing sulfuric acid with the mother liquor to obtain a dissolved product of nitroaniline, wherein the purity is 97.3% and the yield is 97.1% through chromatographic analysis.
Furthermore, it should be understood that various changes and modifications can be made by one skilled in the art after reading the above description of the present invention, and equivalents also fall within the scope of the invention as defined by the appended claims.
Claims (4)
1. A continuous process for the chlorination of nitroaniline, comprising: dissolving 2,4-dinitroaniline in 98wt% sulfuric acid to obtain a sulfuric acid solution of 2,4-dinitroaniline, wherein the mass ratio of 2,4-dinitroaniline to 98wt% sulfuric acid is 1; the solution and the chlorine are respectively conveyed to a micro-mixing reactor through a constant flow pump and a gas flowmeter, and the molar ratio of 2,4-dinitroaniline to the chlorine is 1.60; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 50 ℃, the pressure is 0.4MPa, and the retention time is 2h; dividing the material obtained by the reaction into a backflow material and a finished material by a flow division ratio 7:1 through a circulation unit three-way valve; conveying the reflux material to a micro-mixing reactor, and mixing the reflux material with reaction raw materials; after the material flow passes through a gas collection unit, redundant chlorine and hydrogen chloride generated in the reaction are recovered, the temperature is reduced to 0 ℃, a product is crystallized and separated out from the solution, further solid-liquid separation is carried out to obtain 2,4-dinitro-6-chloroaniline, and mother liquor is circulated to replace sulfuric acid for dissolving nitroaniline; the product was analyzed by chromatography with a purity of 97.1% and a yield of 97.0%.
2. A continuous process for the chlorination of nitroaniline, comprising: dissolving paranitroaniline in 95wt% sulfuric acid to obtain a sulfuric acid solution of the paranitroaniline, wherein the mass ratio of the paranitroaniline to the 95wt% sulfuric acid is 1:3, and the temperature of the solution is controlled at 35 ℃; the solution and chlorine are respectively conveyed to a supergravity reactor through an advection pump and a gas flowmeter, and the molar ratio of the paranitroaniline to the chlorine is 1; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 35 ℃, the pressure is 0.2MPa, and the retention time is 2.5h; dividing the material obtained by the reaction into a backflow material and a finished material by a flow division ratio 8:1 through a circulation unit three-way valve; conveying the reflux material to a supergravity reactor, and mixing the reflux material with reaction raw materials; after the material flow passes through a gas collection unit, redundant chlorine and hydrogen chloride generated in the reaction are recovered, the temperature is reduced to 2 ℃, a product is crystallized and separated out from the solution, the o-chloro-p-nitroaniline is obtained through further solid-liquid separation, and the mother liquor is circulated to replace sulfuric acid for dissolving nitroaniline; the product was analyzed by chromatography with a purity of 98.5% and a yield of 98.2%.
3. A continuous process for the chlorination of nitroaniline, comprising: dissolving p-nitroaniline in 98wt% sulfuric acid to obtain a sulfuric acid solution of the p-nitroaniline, wherein the mass ratio of the p-nitroaniline to the 98wt% sulfuric acid is 1; the solution and the chlorine are respectively conveyed to a micro-mixing reactor through an advection pump and a gas flowmeter, and the molar ratio of the p-nitroaniline to the chlorine is 1.53; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 39 ℃, the pressure is 0.2MPa, and the retention time is 2.5h; dividing the material obtained by the reaction into a backflow material and a finished material by a flow division ratio 7:1 through a circulation unit three-way valve; conveying the reflux material to a micro-mixing reactor, and mixing the reflux material with reaction raw materials; after the material flow passes through a gas collection unit, redundant chlorine and hydrogen chloride generated in the reaction are recovered, the temperature is reduced to 0 ℃, a product is crystallized and separated out from the solution, the o-chloro-p-nitroaniline is obtained through further solid-liquid separation, and the mother liquor is circulated to replace sulfuric acid for dissolving nitroaniline; the product was analyzed by chromatography with 98.0% purity and 97.8% yield.
4. A continuous process for the chlorination of nitroaniline, comprising: 2,4-dinitroaniline is dissolved in 96wt% sulfuric acid to obtain a sulfuric acid solution of 2,4-dinitroaniline, the mass ratio of 2,4-dinitroaniline to 96wt% sulfuric acid is 1:3, and the solution temperature is controlled to be 53 ℃; the solution and the chlorine are respectively conveyed to a micro-mixing reactor through a constant flow pump and a gas flowmeter, and the molar ratio of 2,4-dinitroaniline to the chlorine is 1.58; the materials are mixed and then enter a tubular reactor for reaction, the reaction temperature is controlled at 54 ℃, the pressure is 0.4MPa, and the retention time is 2h; dividing the material obtained by the reaction into a backflow material and a finished material by a flow division ratio 7:1 through a circulation unit three-way valve; conveying the reflux material to a micro-mixing reactor, and mixing the reflux material with reaction raw materials; after the material flow passes through a gas collection unit, redundant chlorine and hydrogen chloride generated in the reaction are recovered, the temperature is reduced to 0 ℃, a product is crystallized and separated out from the solution, further solid-liquid separation is carried out to obtain 2,4-dinitro-6-chloroaniline, and mother liquor is circulated to replace sulfuric acid for dissolving nitroaniline; the product was analyzed by chromatography with a purity of 97.3% and a yield of 97.1%.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101343232A (en) * | 2008-08-21 | 2009-01-14 | 苏州市罗森助剂有限公司 | Preparation method of o-chloro-p-nitroaniline |
| CN103539680A (en) * | 2013-10-23 | 2014-01-29 | 浙江闰土研究院有限公司 | Clean production process of 6-chloro-2,4-dinitroaniline |
| CN104592042A (en) * | 2014-12-29 | 2015-05-06 | 浙江龙盛集团股份有限公司 | Clean technology for continuously synthesizing 2,4-binitro-6-chloroaniline |
| CN105367428A (en) * | 2015-11-10 | 2016-03-02 | 浙江龙盛集团股份有限公司 | Synthetic technology for 2-chloro-4,6-dinitroaniline |
-
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101343232A (en) * | 2008-08-21 | 2009-01-14 | 苏州市罗森助剂有限公司 | Preparation method of o-chloro-p-nitroaniline |
| CN103539680A (en) * | 2013-10-23 | 2014-01-29 | 浙江闰土研究院有限公司 | Clean production process of 6-chloro-2,4-dinitroaniline |
| CN104592042A (en) * | 2014-12-29 | 2015-05-06 | 浙江龙盛集团股份有限公司 | Clean technology for continuously synthesizing 2,4-binitro-6-chloroaniline |
| CN105367428A (en) * | 2015-11-10 | 2016-03-02 | 浙江龙盛集团股份有限公司 | Synthetic technology for 2-chloro-4,6-dinitroaniline |
Non-Patent Citations (1)
| Title |
|---|
| 2,6―二氯―4―硝基苯胺的合成;周家永等;《化工技术与开发》(第04期);第7页右栏1直接氯化法 * |
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